A process for producing an optically active, fluorine-containing, benzyl alcohol by optically resolving a phthalate half ester of racemic, fluorine-containing, benzyl alcohol by an optically active 1-phenylethylamine and then by hydrolyzing the ester group is publicly known (Non-patent Publication 1 and Non-patent Publication 2).
On the other hand, the following process is disclosed in Non-patent Publication 1 and Non-patent Publication 2 as a process for preparing “a phthalate half ester of racemic, fluorine-containing, benzyl alcohol” which is the starting compound of the process.
That is, in Non-patent Publication 1, a process is taken (the following scheme) in which a fluorine-containing benzaldehyde is reacted with an alkyl Grignard reagent to obtain a magnesium alkoxide of racemic, fluorine-containing, benzyl alcohol, then the magnesium alkoxide is converted to a racemic, fluorine-containing, benzyl alcohol, then the racemic, fluorine-containing, benzyl alcohol is once isolated and purified, and then under a basic condition it is reacted with phthalic anhydride (the following scheme).

On the other hand, in Non-patent Publication 2, a process is taken (the following scheme) in which an aliphatic aldehyde is reacted with a fluorine-containing phenyl Grignard reagent, thereby converting it to a magnesium alkoxide of racemic, fluorine-containing, benzyl alcohol, and subsequently it is reacted directly with phthalic anhydride.
Non-patent Publication 1: Journal of the American Chemical Society (US), 1990, Vol. 112, No. 15, p. 5741-5747Non-patent Publication 2: Journal of the American Chemical Society (US), 1985, Vol. 107, No. 15, p. 4513-4519